Q&A: Isaac Sacolick on Taking Risks and Leading Digital Transformation—in 2020 and Beyond

We recently caught up with Isaac Sacolick, the founder and president of StarCIO. Isaac’s diverse career has focused on leading digital transformation within organizations and helping others to do the same. He is the author of the Amazon bestseller Driving Digital: The Leader’s Guide to Business Transformation through Technology.

Digital Transformation Requirements: Risk Taking, Knowledge Sharing

Treasure Data: You describe yourself as a teacher, guide, and advisor, and your work includes writing about technology, speaking at events, running workshops, and diving deep into technology implementations. How did you land such a cool job? And what advice would you give to others who want to follow in your footsteps?

Isaac: My advice is to lead by example, take intelligent risks, and share your knowledge.

I jumped at every leadership role that was in front of me. I was a startup CTO for a decade and then worked as a CIO in transforming enterprises for another decade all in diverse industries including media, financial services, construction, and travel. While leading organizations and teams, I wasn’t afraid of taking risks, rolling up my sleeves to work directly with technologies, and challenging the status quo. I gravitated to companies and industries where transformation was beckoning and evolved my strategies, leadership approaches, and practices that helped people adapt to change and address new opportunities.

I also didn’t keep my learnings to myself, because I realized that transforming organizations required active technology brand ambassadors. I started blogging in 2005, speaking in 2008, and running customer advisory panels in 2010. I now have over five hundred articles published and an Amazon bestselling book Driving Digital.

Treasure Data: With all of the change happening now, how does an enterprise avoid getting disrupted?

Isaac: You can’t avoid disruption, you have to plot a course to a digital future. Guarding organizational sacred cows and maintaining profit margins on legacy products and services is a recipe for disruption. That means having useful data and insights on where markets are heading, what key customer segments are valuing, and how to deliver incremental improvements to digital and data-driven products and services.

For most organizations, it requires a significant culture change that needs to be instrumented bottom-up and top-down to be successful. For most organizations, it means investing in agile practices and product management, and becoming data-driven. I discuss these three primary topics in my book, and my company, StarCIO, advises clients, guides transformations, and leads workshops on these critical areas.

Treasure Data: How can technology leaders develop a more data-centric business?

Isaac: There also needs to be an organized change-management program to help everyone in the business leverage data in decision making.

Leaders must stop looking at data and analytics through the lens of PowerPoint and spreadsheets. Technology leaders have to pave the way by making integrated, cleansed, and near-real-time data and analytics easily consumable by executives, leaders, and individuals.

Treasure Data: What’s the one mistake you think companies are making today with regards to their data?

Isaac: Data and technology leaders often make the mistake of trying to get all the platforms, infrastructure, and data governance in place before exposing data and analytics to more leaders and employees.

It’s a mistake, because these data and technology disciplines need to be invested in parallel to share the analytics and seek early adopters. Organizations should expose non-sensitive data and analytics to a broad audience to get feedback, encourage questions, and drive curiosity. Data leaders must expose the data-quality issues and create business need to improve it. Technology leaders need to be prepared to iterate and improve platforms and governance.

Treasure Data: How can data help companies get a 360-degree view of their customers?

Isaac: We used to think about customer segmentation around a handful of dimensions. To be competitive today, organizations need clean data, algorithms to identify buying signals, and machine learning to identify customer segments and how best to engage them.

There is significant context that should be captured around an organization’s customers to effectively develop relationships with them, market them the most appropriate product and services, and reach them at the most opportune times and spaces—with the right messaging. It’s a significant challenge for marketers to cut through the noise, but also not deluge customers with the wrong messages at the wrong time.

Treasure Data: What are you most excited about as a technology leader today?

Isaac: I’m most excited about bringing technology and data capabilities to wider audiences. It’s clear that the largest technology companies have significant advantages over other businesses when it comes to their data, access to technology, and the ability to recruit talent. But there are also opportunities for small, medium, and larger companies to develop technology and data capabilities that improve competitiveness and drive growth.

Treasure Data: What do you predict will be the most important technology trend in 2020 and beyond?

Isaac: We’re still relatively early on the commercial potential and impacts of machine learning and artificial intelligence. I studied both in my graduate school days, and there remain significant opportunities in areas like natural language processing, recommendation engines, and reinforcement learning that many businesses have not experimented with yet.

Ready to Empower Your Organization with Data?

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Isaac Sacolick, President of StarCIO, is the author of the Amazon bestseller Driving Digital: The Leader’s Guide to Business Transformation through Technology which covers many practices such as agile, devops, and data science that are critical to successful digital transformation programs. Sacolick is a recognized top social CIO, digital transformation influencer, and contributing editor at InfoWorld, CIO.com, and Social, Agile and Transformation. When not on the road, Sacolick spends his time with his family and enjoys being outdoors, biking, hiking, skiing, and kayaking.